78808-40-9

Upstream product

• 16156-58-4 prop-2-yn-1-ol methanesulfonate 
• 34713-70-7 2-Phenylpropanal 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 106-96-7 propargyl bromide 

Relevant academic research and scientific papers

Synthesis, characterization of active Sn(0), and its application in selective propargylation of aldehyde at room temperature in water

Active Sn(0) particles are synthesized in high yields by the chemical reduction of the blue-black stannous oxide using freshly prepared sodium stannite solution as reducing agent at 40 °C and 60 °C. The Sn(0) particles are characterized using powder XRD, SEM, and DSC. The as-synthesized Sn(0) particles are applied as reagent for the regioselective synthesis of homopropargyl alcohols from propargyl bromide and aldehydes in distilled water at room temperature (in 50%-84% yields). No assistance of heat, microwave, ultrasound, organic co-solvent, co-reagent, or inert atmosphere is required for this reaction. The propargylation reaction is highly chemoselective towards aldehyde over other less electrophilic carbonyl functional groups such as ketone, amide, and carboxylic acid. Our in-house synthesized homopropargyl alcohols can be used to synthesize conjugated 1,3-diynes.

Carbonyl propargylation and allenylation with 2-propynyl mesylates, tin(IV) iodide, and tetrabutylammonium iodide controlled by either a steric effect or coordination effect

A combination of tin(IV) iodide and tetrabutylammonium iodide can be used for propargylation or allenylation of aldehydes with 2-propynyl mesylates in dichloromethane. 1-Methyl-2-propynyl mesylate or 2-butynyl mesylate results in propargylation or allenyl

Highly efficient water promoted allylation and propargylation of arylepoxides via rearrangement-carbonyl addition

A simple and highly efficient one-pot procedure for allylation and propargylation of arylepoxides has been developed. A combination of SnCl 2 and catalytic Pd(0) or Pd(II) promotes the reaction of organic halides and epoxides in DMSO with controlled water addition, leading to the regioselective formation of the corresponding homoallyl and homopropargyl alcohols in good yields.

Tuning the reactivity of organotin(IV) by LiOH: Allylation and propargylation of epoxides via redox transmetalation

In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant.

A CONVENIENT SYNTHESIS OF α-HYDROXYALLENES BY THE REACTION OF PROPARGYL IODIDES WITH ALDEHYDES IN THE PRESENCE OF STANNOUS HALIDE

In the presence of stannous halide, propargyl iodides react with aldehydes in an aprotic solvent to yield α-hydroxyallenes as major products, particularly in the cases of γ-substituted propargyl iodides, along with β-hydroxyacetylenes.